ethyl 5-nitrobenzo[d]oxazole-2-carboxylate | 1159515-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: ethyl 5-nitrobenzo[d]oxazole-2-carboxylate
• 英文别名: 2-Benzoxazolecarboxylic acid, 5-nitro-, ethyl ester；ethyl 5-nitro-1,3-benzoxazole-2-carboxylate
• CAS: 1159515-90-8
• 化学式: C₁₀H₈N₂O₅
• 分子量: 236.184
• InChiKey: XDFFACVVLUBJMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  373.9±34.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-nitrobenzo[d]oxazole-2-carboxylate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-N-(1-methylpiperidin-4-yl)benzo[d]oxazole-2-carboxamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway

  摘要：

  Pancreatic ductal adenocarcinoma (PDAC) is one of the most common type of pancreatic cancer, and has still been the medicinal mystery. New drugs and treatment strategies are urgently needed. In this study, 32 benzofuran derivatives are designed, synthesized and evaluated as potential agents against the pancreatic cancer. Among them, compound 9o with the best physicochemical and pharmacokinetic properties exhibited excellent cytotoxicity against many tumor cell lines. In vivo study showed that compound 9o dramatically suppressed the tumor growth of nude mice. Furthermore, compound 9o could affect the hypoxia environment through Hif-1 alpha/VEGF pathway, resulting in the anti-angiogenic activity. These studies indicated that compound 9o was a promising candidate for the treatment of PDAC, deserving further studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.05.042
• 作为产物：
  描述：

  草酸二乙酯 、 2-氨基-4-硝基苯酚 在 sodium docusate 作用下， 以 水 为溶剂， 反应 2.5h， 以96%的产率得到ethyl 5-nitrobenzo[d]oxazole-2-carboxylate
  参考文献：
  名称：

  在水介质中2-氨基苯硫酚/苯酚/苯胺与1,2-双亲电子试剂的环缩合反应中苯并-2-羧酸酯与苯并3-酮/苯并-2,3-二酮选择性开关的合理化

  摘要：

  的2-氨基苯硫酚与1,2- biselectrophiles如乙醛酸乙酯和草酸二乙酯在水性介质中的引线经由5-形成苯并噻唑-2-羧酸酯的环化缩合反应内切- trig的过程相反Baldwin的规则。另一方面，2-氨基苯酚/苯胺的反应通过6- exo - trig生成了相应的benzazine-3-ones或benzazine-2,3-diones。符合鲍德温规则的流程。使用硬-软酸碱原理，量子化学计算（密度泛函理论）和轨道相互作用研究对这些环缩合反应的机理进行了深入研究，从而使苯并噻唑-2-羧酸酯与苯并三嗪-3-ones / benzazine-2的选择性转换合理化。 ，3-二酮。水的存在通过降低能垒来促进这些环缩合反应。

  DOI：

  10.1021/acs.joc.7b01548

文献信息

• Rationalization of Benzazole-2-carboxylate versus Benzazine-3-one/Benzazine-2,3-dione Selectivity Switch during Cyclocondensation of 2-Aminothiophenols/Phenols/Anilines with 1,2-Biselectrophiles in Aqueous Medium
  作者：Tejas M. Dhameliya、Sumit S. Chourasiya、Eshan Mishra、Pradeep S. Jadhavar、Prasad V. Bharatam、Asit K. Chakraborti

  DOI：10.1021/acs.joc.7b01548

  日期：2017.10.6

  insights of these cyclocondensation reactions using the hard–soft acid–base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.

  的2-氨基苯硫酚与1,2- biselectrophiles如乙醛酸乙酯和草酸二乙酯在水性介质中的引线经由5-形成苯并噻唑-2-羧酸酯的环化缩合反应内切- trig的过程相反Baldwin的规则。另一方面，2-氨基苯酚/苯胺的反应通过6- exo - trig生成了相应的benzazine-3-ones或benzazine-2,3-diones。符合鲍德温规则的流程。使用硬-软酸碱原理，量子化学计算（密度泛函理论）和轨道相互作用研究对这些环缩合反应的机理进行了深入研究，从而使苯并噻唑-2-羧酸酯与苯并三嗪-3-ones / benzazine-2的选择性转换合理化。 ，3-二酮。水的存在通过降低能垒来促进这些环缩合反应。
• Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway
  作者：Xiao-li Xu、Ying-rui Yang、Xiao-fei Mo、Jin-lian Wei、Xiao-jin Zhang、Qi-dong You

  DOI：10.1016/j.ejmech.2017.05.042

  日期：2017.9

  Pancreatic ductal adenocarcinoma (PDAC) is one of the most common type of pancreatic cancer, and has still been the medicinal mystery. New drugs and treatment strategies are urgently needed. In this study, 32 benzofuran derivatives are designed, synthesized and evaluated as potential agents against the pancreatic cancer. Among them, compound 9o with the best physicochemical and pharmacokinetic properties exhibited excellent cytotoxicity against many tumor cell lines. In vivo study showed that compound 9o dramatically suppressed the tumor growth of nude mice. Furthermore, compound 9o could affect the hypoxia environment through Hif-1 alpha/VEGF pathway, resulting in the anti-angiogenic activity. These studies indicated that compound 9o was a promising candidate for the treatment of PDAC, deserving further studies. (C) 2017 Elsevier Masson SAS. All rights reserved.